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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:44:16 UTC

Update Date

2022-03-07 02:57:13 UTC

HMDB ID

HMDB0041856

Secondary Accession Numbers

HMDB41856

Metabolite Identification

Common Name

Chlorpyrifos

Description

A study of the effects of chlorpyrifos on humans exposed over time showed that people exposed to high levels have autoimmune antibodies that are common in people with autoimmune disorders. There is a strong correlation to chronic illness associated with autoimmune disorders after exposure to chlorpyrifos. Among 50 farm pesticides studied, chlorpyrifos was one of two found to be associated with higher risks of lung cancer among frequent pesticide applicators than among infrequent or non-users. Pesticide applicators as a whole were found to have a 50% lower cancer risk than the general public, which is attributable to the nearly 50% lower smoking rate found among farm workers. However, applicators of chlorpyrifos had a 15% lower cancer risk than the general public, which the study suggests indicates a likely link between chlorpyrifos application and lung cancer. Chlorpyrifos (IUPAC name: O,O-diethyl O-3,5,6-trichloropyridin-2-yl phosphorothioate) is a crystalline organophosphate insecticide. It was introduced in 1965 by Dow Chemical Company and is known by many trade names (see table), including Dursban and Lorsban. It acts on the nervous system of insects by inhibiting acetylcholinesterase. Chlorpyrifos is an organophosphate, with potential for both acute toxicity at larger amounts and neurological effects in fetuses and children even at very small amounts. For acute effects, the EPA classifies chlorpyrifos as Class II: moderately toxic. The oral LD50 for chlorpyrifos in experimental animals is 32 to 1000 mg/kg. The dermal LD50 in rats is greater than 2000 mg/kg and 1000 to 2000 mg/kg in rabbits. The 4-hour inhalation LC50 for chlorpyrifos in rats is greater than 200 mg/m3. First registered in 1965 and marketed by Dow Chemical under the tradenames Dursban, Lorsban and Renoban, chlorpyrifos was a well known home and garden insecticide, and at one time it was one of the most widely used household pesticides in the US.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0041856
     RDKit          3D
Chlorpyrifos
 29 29  0  0  0  0  0  0  0  0999 V2000
   -2.7767   -2.9199   -0.2685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6253   -2.2169   -0.9156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9906   -0.8344   -1.1649 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7191   -0.0083   -0.3484 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.2841   -0.4464    1.3590 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9250    1.6337   -0.4162 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2521    1.9740   -0.3243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1546    3.5436   -0.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7407   -0.6832   -0.6642 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0203   -0.5465   -0.2143 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0923   -1.1437   -0.6956 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3740   -0.9766   -0.2657 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7932   -1.6836   -0.9219 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.5751   -0.0774    0.8119 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2329    0.3551    1.3015 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.5099    0.5528    1.3684 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2730    0.3160    0.8522 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9394    1.1125    1.5806 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.9084   -3.9166   -0.6292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7247   -2.3476   -0.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4315   -3.0809    0.8551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6967   -2.2857   -0.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5932   -2.6585   -1.9922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7974    1.7909   -1.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7771    1.6312    0.5212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7488    3.9613   -0.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6522    3.7799    0.9009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1337    3.8928   -0.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6404    1.2821    2.1950 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  4  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 17 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  8 28  1  0
 16 29  1  0
M  END


  Mrv1652307282022162D          

 18 18  0  0  0  0            999 V2000
   -1.6500   -0.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.9355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -2.3645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  5  2  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 10  6  1  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  8  2  0  0  0  0
 13  9  1  0  0  0  0
 14  3  1  0  0  0  0
 15  4  1  0  0  0  0
 16  9  1  0  0  0  0
 17 14  1  0  0  0  0
 17 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041856

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOP(=S)(OCC)OC1=C(Cl)C=C(Cl)C(Cl)=N1

> <INCHI_IDENTIFIER>
InChI=1S/C9H11Cl3NO3PS/c1-3-14-17(18,15-4-2)16-9-7(11)5-6(10)8(12)13-9/h5H,3-4H2,1-2H3

> <INCHI_KEY>
SBPBAQFWLVIOKP-UHFFFAOYSA-N

> <FORMULA>
C9H11Cl3NO3PS

> <MOLECULAR_WEIGHT>
350.586

> <EXACT_MASS>
348.926283546

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
30.40435303053504

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
O,O-diethyl O-3,5,6-trichloropyridin-2-yl phosphorothioate

> <ALOGPS_LOGP>
5.15

> <JCHEM_LOGP>
4.784318596666666

> <ALOGPS_LOGS>
-5.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.240655217786368

> <JCHEM_POLAR_SURFACE_AREA>
40.58

> <JCHEM_REFRACTIVITY>
78.9968

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.45e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
terial

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041856
     RDKit          3D
Chlorpyrifos
 29 29  0  0  0  0  0  0  0  0999 V2000
   -2.7767   -2.9199   -0.2685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6253   -2.2169   -0.9156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9906   -0.8344   -1.1649 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7191   -0.0083   -0.3484 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.2841   -0.4464    1.3590 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9250    1.6337   -0.4162 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2521    1.9740   -0.3243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1546    3.5436   -0.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7407   -0.6832   -0.6642 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0203   -0.5465   -0.2143 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0923   -1.1437   -0.6956 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3740   -0.9766   -0.2657 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7932   -1.6836   -0.9219 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.5751   -0.0774    0.8119 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2329    0.3551    1.3015 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.5099    0.5528    1.3684 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2730    0.3160    0.8522 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9394    1.1125    1.5806 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.9084   -3.9166   -0.6292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7247   -2.3476   -0.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4315   -3.0809    0.8551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6967   -2.2857   -0.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5932   -2.6585   -1.9922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7974    1.7909   -1.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7771    1.6312    0.5212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7488    3.9613   -0.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6522    3.7799    0.9009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1337    3.8928   -0.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6404    1.2821    2.1950 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  4  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 17 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  8 28  1  0
 16 29  1  0
M  END

HEADER    PROTEIN                                 28-JUL-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-JUL-20         0                                  
HETATM    1  C   UNK     0      -3.080  -0.413   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.770  -7.081   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.310  -1.746   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -5.747   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10 Cl   UNK     0       1.334   3.850   0.000  0.00  0.00          Cl+0
HETATM   11 Cl   UNK     0       4.001  -0.770   0.000  0.00  0.00          Cl+0
HETATM   12 Cl   UNK     0      -1.334   2.310   0.000  0.00  0.00          Cl+0
HETATM   13  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0      -0.770  -1.746   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       0.770  -4.414   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   17  P   UNK     0       0.000  -3.080   0.000  0.00  0.00           P+0
HETATM   18  S   UNK     0      -1.334  -3.850   0.000  0.00  0.00           S+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1   14                                                       
CONECT    4    2   15                                                       
CONECT    5    6    7                                                       
CONECT    6    5    8   10                                                  
CONECT    7    5    9   11                                                  
CONECT    8    6   12   13                                                  
CONECT    9    7   13   16                                                  
CONECT   10    6                                                            
CONECT   11    7                                                            
CONECT   12    8                                                            
CONECT   13    8    9                                                       
CONECT   14    3   17                                                       
CONECT   15    4   17                                                       
CONECT   16    9   17                                                       
CONECT   17   14   15   16   18                                             
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0041856
HETATM    1  C1  UNL     1      -2.777  -2.920  -0.268  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.625  -2.217  -0.916  1.00  0.00           C  
HETATM    3  O1  UNL     1      -1.991  -0.834  -1.165  1.00  0.00           O  
HETATM    4  P1  UNL     1      -0.719  -0.008  -0.348  1.00  0.00           P  
HETATM    5  S1  UNL     1      -1.284  -0.446   1.359  1.00  0.00           S  
HETATM    6  O2  UNL     1      -0.925   1.634  -0.416  1.00  0.00           O  
HETATM    7  C3  UNL     1      -2.252   1.974  -0.324  1.00  0.00           C  
HETATM    8  C4  UNL     1      -2.155   3.544  -0.080  1.00  0.00           C  
HETATM    9  O3  UNL     1       0.741  -0.683  -0.664  1.00  0.00           O  
HETATM   10  C5  UNL     1       2.020  -0.547  -0.214  1.00  0.00           C  
HETATM   11  N1  UNL     1       3.092  -1.144  -0.696  1.00  0.00           N  
HETATM   12  C6  UNL     1       4.374  -0.977  -0.266  1.00  0.00           C  
HETATM   13 CL1  UNL     1       5.793  -1.684  -0.922  1.00  0.00          CL  
HETATM   14  C7  UNL     1       4.575  -0.077   0.812  1.00  0.00           C  
HETATM   15 CL2  UNL     1       6.233   0.355   1.302  1.00  0.00          CL  
HETATM   16  C8  UNL     1       3.510   0.553   1.368  1.00  0.00           C  
HETATM   17  C9  UNL     1       2.273   0.316   0.852  1.00  0.00           C  
HETATM   18 CL3  UNL     1       0.939   1.112   1.581  1.00  0.00          CL  
HETATM   19  H1  UNL     1      -2.908  -3.917  -0.629  1.00  0.00           H  
HETATM   20  H2  UNL     1      -3.725  -2.348  -0.160  1.00  0.00           H  
HETATM   21  H3  UNL     1      -2.431  -3.081   0.855  1.00  0.00           H  
HETATM   22  H4  UNL     1      -0.697  -2.286  -0.437  1.00  0.00           H  
HETATM   23  H5  UNL     1      -1.593  -2.658  -1.992  1.00  0.00           H  
HETATM   24  H6  UNL     1      -2.797   1.791  -1.266  1.00  0.00           H  
HETATM   25  H7  UNL     1      -2.777   1.631   0.521  1.00  0.00           H  
HETATM   26  H8  UNL     1      -2.749   3.961  -0.894  1.00  0.00           H  
HETATM   27  H9  UNL     1      -2.652   3.780   0.901  1.00  0.00           H  
HETATM   28  H10 UNL     1      -1.134   3.893  -0.088  1.00  0.00           H  
HETATM   29  H11 UNL     1       3.640   1.282   2.195  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   22   23
CONECT    3    4
CONECT    4    5    5    6    9
CONECT    6    7
CONECT    7    8   24   25
CONECT    8   26   27   28
CONECT    9   10
CONECT   10   11   11   17
CONECT   11   12
CONECT   12   13   14   14
CONECT   14   15   16
CONECT   16   17   17   29
CONECT   17   18
END

HMDB0041856
     RDKit          3D
Chlorpyrifos
 29 29  0  0  0  0  0  0  0  0999 V2000
   -2.7767   -2.9199   -0.2685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6253   -2.2169   -0.9156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9906   -0.8344   -1.1649 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7191   -0.0083   -0.3484 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.2841   -0.4464    1.3590 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9250    1.6337   -0.4162 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2521    1.9740   -0.3243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1546    3.5436   -0.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7407   -0.6832   -0.6642 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0203   -0.5465   -0.2143 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0923   -1.1437   -0.6956 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3740   -0.9766   -0.2657 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7932   -1.6836   -0.9219 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.5751   -0.0774    0.8119 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2329    0.3551    1.3015 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.5099    0.5528    1.3684 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2730    0.3160    0.8522 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9394    1.1125    1.5806 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.9084   -3.9166   -0.6292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7247   -2.3476   -0.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4315   -3.0809    0.8551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6967   -2.2857   -0.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5932   -2.6585   -1.9922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7974    1.7909   -1.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7771    1.6312    0.5212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7488    3.9613   -0.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6522    3.7799    0.9009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1337    3.8928   -0.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6404    1.2821    2.1950 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  4  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 17 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  8 28  1  0
 16 29  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Bolton	ChEBI
Brodan	ChEBI
Chlorpyrifos ethyl	ChEBI
Chlorpyrifos-ethyl	ChEBI
Chlorpyriphos	ChEBI
Cobalt	ChEBI
Detmol	ChEBI
Dowco 179	ChEBI
Dursban	ChEBI
Empire	ChEBI
Equity	ChEBI
Eradex	ChEBI
Lentrek	ChEBI
Lock-ON	ChEBI
Lorsban	ChEBI
m-Chlorpyrifos	ChEBI
Nufos	ChEBI
O,O-Diethyl O-(3,5,6-trichloropyridin-2-yl) thiophosphate	ChEBI
O,O-Diethyl-O-(3,5,6-trichloro-2-pyridyl)phosphorothioate	ChEBI
Phosphorothioic acid, O,O-diethyl O-(3,5,6-trichloro-2-pyridinyl) ester	ChEBI
Piridane	ChEBI
Stipend	ChEBI
Tricel	ChEBI
Trichlorpyrphos	ChEBI
Warhawk	ChEBI
Zodiac	Kegg
O,O-Diethyl O-(3,5,6-trichloropyridin-2-yl) thiophosphoric acid	Generator
O,O-Diethyl-O-(3,5,6-trichloro-2-pyridyl)phosphorothioic acid	Generator
Phosphorothioate, O,O-diethyl O-(3,5,6-trichloro-2-pyridinyl) ester	Generator
Bonidel	HMDB
Chloropyrifos	HMDB
Chloropyriphos	HMDB
Chlorpyriphos-ethyl	HMDB
Chlorpyrofos	HMDB
Chlorpyrophos	HMDB
Coroban	HMDB
Danusban	HMDB
Detmol u.a.	HMDB
Durmet	HMDB
Dursban 10CR	HMDB
Dursban 2E	HMDB
Dursban 4E	HMDB
Dursban F	HMDB
Dursban R	HMDB
Empire 20	HMDB
Ethyl chlorpyriphos	HMDB
Geodinfos	HMDB
Killmaster	HMDB
O,O-Diaethyl-O-3,5,6-trichlor-2-pyridylmonothiophosphat	HMDB
O,O-Diethyl O-(3,5,6-trichloro-2-pyridinyl)phosphorothioate	HMDB
O,O-Diethyl O-(3,5,6-trichloro-2-pyridyl) phosphorothioate	HMDB
O,O-Diethyl O-(3,5,6-trichloropyridin-2-yl) phosphorothioate	HMDB
Pageant	HMDB
Pyrinex	HMDB
Radar	HMDB
Silrifos	HMDB
Spannit	HMDB
SuSCon	HMDB
Suscon blue	HMDB
Suscon green	HMDB
Tafaban	HMDB
Terial	HMDB
Zidil	HMDB

Chemical Formula

C₉H₁₁Cl₃NO₃PS

Average Molecular Weight

350.586

Monoisotopic Molecular Weight

348.926283546

IUPAC Name

O,O-diethyl O-3,5,6-trichloropyridin-2-yl phosphorothioate

Traditional Name

terial

CAS Registry Number

2921-88-2

SMILES

CCOP(=S)(OCC)OC1=C(Cl)C=C(Cl)C(Cl)=N1

InChI Identifier

InChI=1S/C9H11Cl3NO3PS/c1-3-14-17(18,15-4-2)16-9-7(11)5-6(10)8(12)13-9/h5H,3-4H2,1-2H3

InChI Key

SBPBAQFWLVIOKP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryl thiophosphates. These are organic compounds containing the thiophosphoric acid functional group or a derivative thereof, with the general structure ROP(OR')(OR'')=S, where at least one R-group is an aryl group.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic thiophosphoric acids and derivatives

Sub Class

Thiophosphoric acid esters

Direct Parent

Aryl thiophosphates

Alternative Parents

Substituents

Aryl thiophosphate
Thiophosphate triester
Polyhalopyridine
2-halopyridine
Aryl chloride
Aryl halide
Pyridine
Heteroaromatic compound
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

organic thiophosphate (CHEBI:34631 )
chloropyridine (CHEBI:34631 )
Organophosphorus insecticides (C14322 )
a small molecule (CPD-8963 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	42 °C	Not Available
Boiling Point	375.90 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.0011 mg/mL at 24 °C	Not Available
LogP	4.96	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	201.738	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001306

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0014 g/L	ALOGPS
logP	5.15	ALOGPS
logP	4.78	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	40.58 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	79 m³·mol⁻¹	ChemAxon
Polarizability	30.4 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	165.599	30932474
DeepCCS	[M-H]-	163.241	30932474
DeepCCS	[M-2H]-	196.127	30932474
DeepCCS	[M+Na]+	171.692	30932474
AllCCS	[M+H]+	164.0	32859911
AllCCS	[M+H-H2O]+	161.2	32859911
AllCCS	[M+NH4]+	166.6	32859911
AllCCS	[M+Na]+	167.4	32859911
AllCCS	[M-H]-	159.1	32859911
AllCCS	[M+Na-2H]-	159.3	32859911
AllCCS	[M+HCOO]-	159.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Chlorpyrifos	CCOP(=S)(OCC)OC1=C(Cl)C=C(Cl)C(Cl)=N1	2803.1	Standard polar	33892256
Chlorpyrifos	CCOP(=S)(OCC)OC1=C(Cl)C=C(Cl)C(Cl)=N1	1964.9	Standard non polar	33892256
Chlorpyrifos	CCOP(=S)(OCC)OC1=C(Cl)C=C(Cl)C(Cl)=N1	1961.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Chlorpyrifos EI-B (Non-derivatized)	splash10-0002-2793000000-24fe8c73aae05cb109a6	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Chlorpyrifos EI-B (Non-derivatized)	splash10-0002-2794000000-df67df73c4dd26908db1	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Chlorpyrifos EI-B (Non-derivatized)	splash10-0002-2793000000-24fe8c73aae05cb109a6	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Chlorpyrifos EI-B (Non-derivatized)	splash10-0002-2794000000-df67df73c4dd26908db1	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chlorpyrifos GC-MS (Non-derivatized) - 70eV, Positive	splash10-02vv-4879000000-9255cc8373a5b6df3d65	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chlorpyrifos GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-002b-8972000000-01227c0965379003bd5c	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpyrifos LC-ESI-ITFT , positive-QTOF	splash10-00di-0119000000-40638c6cc56c702af00f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpyrifos LC-ESI-ITFT , positive-QTOF	splash10-0002-0309000000-1c03b781190605e158ab	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpyrifos LC-ESI-ITFT , positive-QTOF	splash10-0002-1920000000-1f0cc45d40a433cd21db	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpyrifos LC-ESI-ITFT , positive-QTOF	splash10-01ot-2910000000-ae08635e79dc0112ef17	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpyrifos LC-ESI-ITFT , positive-QTOF	splash10-01ot-2910000000-b384378ff2454771bc14	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpyrifos LC-ESI-ITFT , positive-QTOF	splash10-01ot-2900000000-3169dbfdf2b277cfa7c0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpyrifos LC-ESI-ITFT , positive-QTOF	splash10-08fs-2900000000-b9485df818d11c39fef7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpyrifos LC-ESI-ITFT , positive-QTOF	splash10-0002-0309000000-e0f5343f2722d612251f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpyrifos LC-ESI-ITFT , positive-QTOF	splash10-0002-1910000000-bfd22e25d1af7f7accb3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpyrifos LC-ESI-ITFT , positive-QTOF	splash10-01ot-2910000000-ba821b94f503bfeb9235	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpyrifos LC-ESI-ITFT , positive-QTOF	splash10-01ot-2900000000-9bb1451e70826e7e9a9f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpyrifos LC-ESI-ITFT , positive-QTOF	splash10-01ot-2900000000-9ce44e25c83ae56e97f0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpyrifos LC-ESI-ITFT , positive-QTOF	splash10-08fs-2900000000-b3d73af1ad2b48fb311b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpyrifos LC-ESI-ITFT , positive-QTOF	splash10-00di-0119000000-ba99c1365306cb006059	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpyrifos ESI-ITFT , positive-QTOF	splash10-006t-0916000000-e5066adbf2b26421940a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpyrifos LC-ESI-QFT , positive-QTOF	splash10-01ot-0912000000-574ee0c0da4a9208c364	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpyrifos 35V, Positive-QTOF	splash10-00di-0119000000-9c6de680a79a370a9448	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpyrifos 35V, Positive-QTOF	splash10-00di-0019000000-8f591ca38c38b7d4aefe	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpyrifos 60V, Positive-QTOF	splash10-01ot-2900000000-f12e60a6223e79be2b2f	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorpyrifos 10V, Positive-QTOF	splash10-006t-0019000000-a09b1f8553c2f9ff157e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorpyrifos 20V, Positive-QTOF	splash10-006x-2198000000-678ca9f31d75ee655aa0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorpyrifos 40V, Positive-QTOF	splash10-0574-9831000000-b360760e7ac0a1382d5e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorpyrifos 10V, Negative-QTOF	splash10-0fr2-0329000000-1c8dc6df96eaf1f4e279	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorpyrifos 20V, Negative-QTOF	splash10-00yl-0595000000-04c8a10e9e94fe0b4a81	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorpyrifos 40V, Negative-QTOF	splash10-000f-0590000000-f8e446946e10066540eb	2016-08-04	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2629

KEGG Compound ID

C14322

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Chlorpyrifos

METLIN ID

Not Available

PubChem Compound

2730

PDB ID

Not Available

ChEBI ID

34631

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1347681

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Chlorpyrifos (HMDB0041856)

MOL for HMDB0041856 (Chlorpyrifos)

3D MOL for HMDB0041856 (Chlorpyrifos)

3D SDF for HMDB0041856 (Chlorpyrifos)

3D-SDF for HMDB0041856 (Chlorpyrifos)

PDB for HMDB0041856 (Chlorpyrifos)

3D PDB for HMDB0041856 (Chlorpyrifos)

SMILES for HMDB0041856 (Chlorpyrifos)

INCHI for HMDB0041856 (Chlorpyrifos)

Structure for HMDB0041856 (Chlorpyrifos)

3D Structure for HMDB0041856 (Chlorpyrifos)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra